


Halloween Costumes

by BuzzBlabs



Category: Critical Role (Web Series)
Genre: Anal Fingering, Anal Plug, Cat boy Caleb, Halloween Porn, Light Dom/sub, M/M, Plot What Plot/Porn Without Plot, no beta we die like men, pet play kinda
Language: English
Status: Completed
Published: 2020-11-01
Updated: 2020-11-01
Packaged: 2021-03-08 22:53:36
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,659
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27324553
Author URL: https://archiveofourown.org/users/BuzzBlabs/pseuds/BuzzBlabs
Summary: This is a shameless fic that the widomauk sever inspired by talking about catboy Caleb. Hope you all enjoy!
Relationships: Mollymauk Tealeaf/Caleb Widogast, Widomauk - Relationship
Comments: 4
Kudos: 123





	Halloween Costumes

Caleb adjusted the fluffy cat ears that sat on his head with a slight frown. How did he let Molly convince him of this? Here he was, standing in front of his full-length mirror with a knee length black dress with a white petty coat underneath it. Atop his head was a cheaply made headband with two black cat ears, and a thin black necklace hung around his neck that had a small bell. The costume idea started as a joke from Jester, but Mollymauk decided that the image of Caleb in a cat costume was too good to pass up. He shifted to try and smoothed down the bouncy fabric. How did Jester stand to wear dresses like this? Even with the thick thigh high socks Caleb felt far too cold.

“Almost ready darling?” Molly’s voice chirped happily from the bathroom.

“If by almost ready you mean ready to die from embarrassment then ja…” Caleb gave a heavy sigh.

“Oh, come on now,” The tiefling popped out from behind the door with a wild grin. “You look amazing!” Molly was wearing a classic Dracula costume, his natural fangs and red eyes complementing the outfit.

“That is easy for you to say, I feel like my ass is going to be exposed all night.”

Molly came up behind him and pulled Caleb into his arms. A wicked grin grew on his face. “That is half the appeal my dear. I think you look amazing~.”

Caleb rolled his eyes dramatically as he turned to face Molly. “Wipe that grin off your face.”

“Mm, no I don’t think I will.” Molly’s hands shifted to grab a handful of the human’s ass. “You really do look amazing, but I can’t help but notice you are missing a piece of your costume darling.”

He thought for a moment then shook his head. “No, I am sure this is the entire outfit that you handed me.”

The wicked grin on Molly’s face only grew. He pulled Caleb closer, his face resting next to his ear. “What if I told you I saved a little surprise?”

A chill ran down Caleb’s spine as the warm breath brushed against his skin. 

“Would you like to see it?”

“Ja. Whatever it is you seem very interested.”

Molly gave Caleb a chaste kiss, quickly pulling away to stride over to his bag. Caleb couldn’t help but nervously worry his lip at the idea that there was more to the costume than originally thought. He was running through costume pieces in his head: ears, collar, the gloves that had the paw designs-

Any thoughts in Caleb’s head came to an immediate stop as Molly turned around. In his hands was a thick black tail that seemed to be the same color as his fur ears. However, that is not what caught his attention. What did was the metal plug that was attached to the end of it. Caleb could feel the blood rush to his face as he sputtered slightly.

“Mollymauk-“ Caleb managed to choke out.

“Obviously we will only do it if you are interested, but I thought it could be fun.” Molly strutted back towards the human. He presented the toy with a hungry look in his eyes.

Caleb ran his fingers over the smooth metal with a shocked expression. Part of him was overwhelmed with anxiety of the idea of wearing something like this in public, but another part of him was insanely turned on about the idea of no one having a clue of what this is. 

“You can say no, Caleb.” The anxiety in Molly’s voice snapped Caleb back into reality. He took Molly’s face into his hands and smashed their lips together. Instantly the tension from Molly’s shoulders seemed to melt away. They lost themselves in the sweet kisses and pressing bodies.

Caleb pulled away to catch his breath, his face flushed. “I want nothing more than for you to put that in me shatz.”

Molly dipped down slightly to capture his boyfriends’ lips in another hungry kiss. Their bodies pressed together as Molly guided Caleb back towards the bed. Molly’s free hand worked its way down his back, past the skirt of the dress and back up to grab at the human’s ass, rewarding him with a groan. Maybe there were some advantages to a dress after all. Once Caleb felt the bed on the back of his legs he fell back, bringing Molly down with him by the collar of his shirt. The tiefling pulled away to trail his lips down to the shell of his ear where he gently nipped and caused Caleb’s breath to hitch.

“Roll over for me and get comfortable kitten,” The nickname sent a wave of arousal straight to Caleb’s cock which caused him to moan softly. The grin on Molly’s face only grew. Once Molly moved his body away Caleb quickly turned himself over to face the mattress. It took only a moment to tuck his legs up underneath him in a comfortable enough way for Molly to get access to what he needed.

Moments later he felt Mollys warm hand return to card through Calebs hair. “Such a good boy.” He cooed lovingly as his other hand slipped back up the dress, this time heading for a different target. Slender fingers ran over Caleb’s half hard cock making him moan and weakly thrust into the touch.

“Shatz, bitte-!”

“Shh…” Molly cooed softly. “Be patient kitten, I know you want it but first we need to finish dressing you up.”

His fingers moved to run over the small of Caleb’s back, pulling his thigh boxer briefs down with him. The hand briefly disappeared and the human let off a pitiful whine at the lack of heat. A moment later the dress was being pushed up to fully expose his ass. Finally, two lube covered fingers began to slowly circle the rim of his asshole. Caleb moaned desperately as he shifted back towards the fingers, he needed more than just light touches.

“So needy,” Molly tsked before a hand gently struck Caleb’s ass, making his cock twitch and another loud moan escape from him. “Such a naughty kitten, can’t even wait. Maybe I should stop?”

“Nien! Bitte, Mollymauk please- I’ll be good!”

“Mm… So pretty when he begs.” Molly chuckled, his finger ever so slightly pressing against his asshole. “Do you think you deserve it?”

“Ja, please-!” Another firm smack cuts him off.

“Please, who?”

“Please sir, please I want your fingers in me! I want you to fuck me with your fingers, I want the tail-!” A sharp gasping moan cut him off as Molly began to slip in a finger.

“Well since you ask so nicely for me kitten~.”

Molly slowly worked in another finger once the first was in, stretching him as his lips ran over Caleb’s neck. Caleb’s cock was to the point that the feeling of his boxers straining against his cock was nearly painful, and he was still desperate for more but it seemed that Molly was nowhere near done with him yet. He opened his mouth to beg for more when Molly crooked his fingers and began to thrust right into his prostate causing only an embarrassingly loud moan to come out. He felt so close to finishing, he was nearly over the brink and read to finish when Molly spoke.

“Do you think you are ready for your tail?”

Caleb attempted to answer but Molly’s fingers contained to pound into his prostate, making his speech broken with moans. He knew the correct answer, even if he was on the edge of release.

“Bitte, ah Molly- B- AH BITTE!” With that Molly pulled out his fingers and Caleb practically chased them with a whine as his orgasm escaped.

“I know darling,” Molly cooed as he gripped the human’s ass. “Just wait a moment and I’ll give you what you want.”

Caleb felt Molly full off his boxers to let his cock free, the cool air being a relief compared to the restraining fabric but the lack of friction was upsetting. Before he had time to vocalize his complaints the head of the metal toy pressed against his asshole and was pushing in. A low moan made his chest rumble as he gently pushed back against the pressure to take in more. Molly chuckled, pressing the toy in until it bottomed out inside Caleb.

A shiver ran over Caleb’s spine with a mean as he felt Molly experimentally tug at the toy. Luckily it didn’t seem in danger of falling out of him anytime soon.

“Such a good boy, you took your new toy so well… How does it feel, darling?”

“Wunderbar, thank you sir.” Caleb managed to whine. He swayed his hips side to side, enjoying the feeling of the weight inside him.

Molly’s hands trailed over his ass, giving him another firmer smack in the process. “You were so good for me kitten, I think you have earned a reward.” His hand came around and finally wrapped around his aching cock. Caleb began to eagerly thrust into Molly’s hand with soft moans, the feeling of an orgasm slowly returning to his core.

“That’s it darling,” He hummed as he kissed Caleb’s neck, his fingers only tightening. “Such a beautiful kitten, so good for me, so eager to please~.”

“J-ja- Molly please-!”

“Go ahead kitten, cum for me.”

Caleb continued to thrust into Molly’s hand with obscene moans until he finally came in Molly’s hand, his whole body shaking as he came down. His boyfriend continued to pump him and lavish his neck with kisses until it was clear he was wrung dry. Only then did Molly pull away with a satisfied grin.

“Well, I am glad you like your new toy.”

Caleb merely gave a weak nod as he attempted to catch his breath.

“Take your time dear, we don’t have to go anywhere until you are ready.”


End file.
